Jiangtao Zhu

Synthesis of 2-fluoroalkylbenzimidazoles via copper(i)-catalyzed tandem reactions

Preparation of 2-fluoroalkylbenzimidazoles from N-aryl trifluoroacetimidoyl (or bromodifluoroacetimidoyl) chlorides and primary amines has been achieved via copper(I)-catalyzed tandem reactions.

Diastereoselective silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with fluorinated imine.

We described hereby an instance of diastereoselective silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with imine compounds. This new method provided synthetically useful, highly substituted tetrahydroimidazole derivatives with efficiency and high diastereoselectivity. We can conveniently obtain fluorinated dihydroimidazole, imidazole, and diamino esters through simple modification.

A New Strategy for the Synthesis of Poly-Substituted 3-H, 3-Fluoro, or 3-Trifluoromethyl Pyridines via the Tandem C-F Bond Cleavage Protocol

A new strategy for the synthesis of poly-substituted 3-H, 3-F, and 3-trifluoromethyl pyridines based on C-F bond breaking of the anionically activated fluoroalkyl group is described. A series of 2,6-disubstituted 4-amino pyridines were prepared through this domino process in high yields under noble metal-free conditions, making this method a supplement to pyridine synthesis.

A general and straightforward method for the synthesis of 2-trifluoromethylbenzothiazoles.

An efficient one-pot method for the synthesis of 2-trifluoromethylbenzothiazoles by the treatment of trifluoromethylimidoyl chlorides with sodium hydrosulfide hydrate using PdCl(2) as the sole catalyst in DMSO is described. The reaction proceeds via thiolation/C-H bond functionalization/C-S bond formation in moderate to high yields with good functional group tolerance.

Synthesis of Fluorine-Containing Multisubstituted Phenanthridines by Rhodium-Catalyzed Alkyne [2+2+2] Cycloaddition and Tandem sp2 CH Difluoromethylenation

A highly efficient method for the synthesis of fluorine-containing multisubstituted phenanthridines through Rh-catalyzed alkyne [2+2+2] cycloaddition reactions has been developed. This method exhibits excellent functional-group compatibility. When a bromodifluoromethyl group, rather than a trifluoromethyl group, was employed in the cycloaddition reaction, more-complicated polycyclic compounds were obtained through tandem Rh-catalyzed cycloaddition/C-H difluoromethylenation. This route provides convenient access to fluorine-containing polycyclic compounds.

A cascade process for the synthesis of gem-difluoromethylene compounds

An efficient strategy for the synthesis of 2,2-difluoro-2,3-dihydrofuran derivatives from β-fluoroalkyl-β-enaminoketones is described. The reaction occurred via an intramolecular halophilic attack-initiated cascade process. A series of 2,3-dihydrofurans were prepared in high yields. And an intermolecular domino process achieved providing polysubstituted furans. The mechanism of the reaction is discussed.